IV. ANHANG 179. Anhang 178

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1 Anhang 178 IV. ANHANG Röntgenstrukturanalysen (Tabellen) Diastereomer A (Diplomarbeit) Diastereomer B (Diplomarbeit) Aldoladdukt 5A Aldoladdukt 13A Aldoladdukt 13B Olefin (E) Aldoladdukt Aldoladdukt 32A Trifluoressigsäurester endocyclisches Olefin 36A Aldoladdukt Aldoladdukt Abkürzungen 278

2 Anhang 179 IV. Anhang 1. Röntgenstrukturanalysen (Tabellen) 1.1. Diastereomer A (Diplomarbeit) Table 1: Crystal data and structure refinement. Empirical formula: C 23 H 33 N O 4 Formula weight: Temperature: 20(2) C Wavelength: Å Crystal system: orthorhombic Space group: P Unit cell dimensions: a = 6.126(2) Å α = 90 deg. b = (4) Å β = 90 deg. c = (4) Å γ = 90 deg. Volume: (10) Å 3 Z: 4 Density (calculated): Mg/m 3 Absorption coefficient: 6.37 cm -1 F(000): 840 Crystal size: 0.38 x 0.25 x 0.16 mm 2 Θ range for data collection: 6.76 to deg. Index ranges: 08h86, 08k818, 08l824 Reflections collected: 1898 Independent reflections: 1898 [R int = ] Refinement method: Full-matrix least-squares on F 2 Data / restraints / parameters: 1898 / 0 / 386

3 Anhang 180 Goodness-of-fit on F 2, S: Final R indices [I>2σ (I)]: R1 = , wr2 = R indices (all data): R1 = , wr2 = Absolute structure parameter: 0.6 (4) Extinction coefficient: (5) Largest diff. peak and hole: and e/å 3 Table 2: Atomic coordinates ( ) and equivalent isotropic displacement parameters (Å ) U(eq) is defined as one third of the trace of the orthogonalized Uij tensor X Y Z U (eq) C(1) -944 (5) 8323 (2) 6036 (1) 57 (1) C(2) -135 (5) 7466 (2) 6252 (1) 49 (1) C(3) -887 (5) 6766 (2) 5829 (1) 50 (1) C(4) -118 (5) 5925 (2) 6044 (1) 49 (1) C(5) -797 (4) 5753 (2) 6705 (1) 45 (1) C(6) 72 (6) 6431 (2) 7117 (1) 54 (1) C(7) -756 (6) 7268 (2) 6915 (1) 52 (1) O(8) 276 (3) 5001 (1) 6919 (1) 48 (1) C(9) -448 (4) 4261 (2) 6760 (1) 42 (1) O(90) 643 (3) 3665 (1) 6878 (1) 52 (1) N(10) (3) 4203 (1) 6459 (1) 42 (1) C(11) (4) 4871 (2) 6401 (1) 46 (1) O(110) (3) 4829 (1) 6081 (1) 65 (1) C(12) (5) 5606 (2) 6770 (1) 48 (1) C(120) (7) 5494 (3) 7429 (2) 65 (1) C(13) (5) 3386 (2) 6272 (1) 47 (1) C(14) (6) 2935 (2) 5830 (1) 53 (1) C(15) (5) 3419 (2) 5262 (1) 48 (1) C(16) (7) 3467 (2) 4783 (2) 67 (1) C(17) (9) 3904 (3) 4263 (2) 84 (1) C(18) -244 (8) 4309 (2) 4212 (2) 82 (1) C(19) 1217 (7) 4274 (2) 4685 (2) 72 (1) C(20) 748 (6) 3831 (2) 5207 (2) 59 (1) C(21) (6) 2865 (2) 6825 (2) 62 (1) O(22) (4) 3300 (2) 7280 (1) 78 (1) C(23) -137 (11) 8494 (3) 5385 (2) 86 (1) C(24) -11 (9) 8986 (2) 6460 (2) 79 (1) C(25) (6) 8384 (3) 6041 (2) 71 (1)

4 Anhang 181 Table 3a: Bond lengths [Å]. C(1)-C(25) (5) N(10)-C(11) (3) C(1)-C(24) (5) N(10)-C(13) (4) C(1)-C(23) (5) C(11)-O(110) (3) C(1)-C(2) (4) C(11)-C(12) (4) C(2)-C(7) (4) C(12)-C(120) (4) C(2)-C(3) (4) C(13)-C(14) (4) C(3)-C(4) (4) C(13)-C(21) (4) C(4)-C(5) (4) C(14)-C(15) (4) C(5)-O(8) (3) C(15)-C(20) (5) C(5)-C(6) (4) C(15)-C(16) (4) C(5)-C(12) (4) C(16)-C(17) (5) C(6)-C(7) (4) C(17)-C(18) (6) O(8)-C(9) (3) C(18)-C(19) (6) C(9)-O(90) (3) C(19)-C(20) (5) C(9)-N(10) (3) C(21)-O(22) (5) Table 3b: Bond angles [deg]. C(25)-C(1)-C(24) (3) C(9)-N(10)-C(11) (2) C(25)-C(1)-C(23) (4) C(9)-N(10)-C(13) (2) C(24)-C(1)-C(23) (4) C(11)-N(10)-C(13) (2) C(25)-C(1)-C(2) (3) O(110)-C(11)-N(10) (3) C(24)-C(1)-C(2) (3) O(110)-C(11)-C(12) (3) C(23)-C(1)-C(2) (3) N(10)-C(11)-C(12) (2) C(7)-C(2)-C(3) (3) C(11)-C(12)-C(5) (2) C(7)-C(2)-C(1) (2) C(11)-C(12)-C(120) (3) C(3)-C(2)-C(1) (2) C(5)-C(12)-C(120) (3) C(4)-C(3)-C(2) (2) N(10)-C(13)-C(14) (2) C(3)-C(4)-C(5) (2) N(10)-C(13)-C(21) (2) O(8)-C(5)-C(6) (2) C(14)-C(13)-C(21) (2) O(8)-C(5)-C(12) (2) C(15)-C(14)-C(13) (2) C(6)-C(5)-C(12) (2) C(20)-C(15)-C(16) (3) O(8)-C(5)-C(4) (2) C(20)-C(15)-C(14) (3) C(6)-C(5)-C(4) (3) C(16)-C(15)-C(14) (3) C(12)-C(5)-C(4) (2) C(17)-C(16)-C(15) (4) C(5)-C(6)-C(7) (2) C(18)-C(17)-C(16) (4) C(6)-C(7)-C(2) (3) C(17)-C(18)-C(19) (4) C(9)-O(8)-C(5) (2) C(18)-C(19)-C(20) (4) O(90)-C(9)-O(8) (2) C(15)-C(20)-C(19) (3) O(90)-C(9)-N(10) (2) O(22)-C(21)-C(13) (3) O(8)-C(9)-N(10) (2)

5 Anhang 182 Table 4: Anisotropic displacement parameters (Å ). The anisotropic displacement factor exponent takes the form: -2π 2. [ h 2. a 2. U h. k. a. b. U 12 ] U11 U22 U33 U23 U13 U12 C(1) 63 (2) 48 (2) 58 (2) 0 (1) 6 (2) 9 (2) C(2) 45 (2) 49 (2) 52 (2) -5 (1) -2 (1) 5 (1) C(3) 56 (2) 50 (2) 44 (2) -5 (1) 2 (1) 6 (2) C(4) 50 (2) 46 (2) 51 (2) -9 (1) 3 (1) 6 (1) C(5) 49 (2) 42 (1) 46 (1) -2 (1) -6 (1) 12 (1) C(6) 60 (2) 52 (2) 49 (2) -5 (1) -13 (2) 6 (2) C(7) 62 (2) 47 (2) 48 (2) -9 (1) -9 (2) 5 (1) O(8) 43 (1) 45 (1) 57 (1) -2 (1) -13 (1) 7 (1) C(9) 39 (1) 46 (1) 42 (1) 1 (1) -2 (1) 6 (1) O(90) 45 (1) 48 (1) 63 (1) 9 (1) -7 (1) 9 (1) N(10) 37 (1) 45 (1) 44 (1) 1 (1) -2 (1) 7 (1) C(11) 38 (1) 54 (2) 46 (1) 0 (1) 2 (1) 8 (1) O(110) 47 (1) 67 (1) 83 (1) -9 (1) -23 (1) 13 (1) C(12) 42 (2) 53 (2) 49 (1) -1 (1) -1 (1) 15 (1) C(120) 63 (2) 76 (2) 55 (2) -2 (2) 10 (2) 16 (2) C(13) 46 (2) 44 (1) 51 (2) 3 (1) -8 (1) 1 (1) C(14) 62 (2) 40 (2) 58 (2) -1 (1) -6 (2) 3 (2) C(15) 56 (2) 38 (1) 51 (2) -10 (1) -2 (1) -1 (1) C(16) 75 (2) 61 (2) 64 (2) -2 (2) -14 (2) -11 (2) C(17) 112 (3) 77 (2) 63 (2) 9 (2) -23 (2) -10 (3) C(18) 120 (3) 58 (2) 67 (2) 7 (2) 8 (2) -8 (3) C(19) 78 (2) 58 (2) 79 (2) -4 (2) 12 (2) -16 (2) C(20) 54 (2) 57 (2) 66 (2) -12 (2) -3 (2) -6 (2) C(21) 49 (2) 69 (2) 69 (2) 15 (2) -2 (2) -7 (2) O(22) 52 (1) 125 (2) 58 (1) 14 (1) 4 (1) 0 (2) C(23) 115 (4) 68 (2) 74 (2) 17 (2) 30 (3) 18 (3) C(24) 101 (3) 46 (2) 91 (3) -6 (2) -1 (3) -6 (2) C(25) 68 (2) 63 (2) 81 (3) 6 (2) -1 (2) 24 (2)

6 Anhang 183 Table 5: Hydrogen coordinates ( ) and isotropic displacement parameters (Å ). X Y Z U H(2) 1603 (59) 7458 (19) 6205 (14) 64 (9) H(31) (55) 6761 (18) 5839 (12) 49 (8) H(32) -342 (48) 6856 (16) 5398 (13) 48 (7) H(41) 1624 (70) 5915 (24) 6057 (17) 89 (12) H(42) -658 (48) 5496 (16) 5775 (11) 42 (7) H(61) 1599 (65) 6404 (21) 7030 (15) 63 (10) H(62) -194 (52) 6285 (17) 7561 (14) 51 (8) H(71) (70) 7329 (20) 6913 (14) 68 (10) H(72) -163 (51) 7679 (17) 7221 (12) 48 (7) H(12) (56) 6043 (18) 6589 (13) 55 (8) H(121) (85) 5273 (28) 7430 (19) 96 (13) H(122) (59) 5082 (22) 7641 (15) 68 (10) H(123) (63) 5983 (23) 7656 (16) 72 (10) H(13) (54) 3515 (18) 6053 (13) 52 (8) H(141) -507 (67) 2772 (21) 6039 (15) 70 (10) H(142) (60) 2419 (20) 5717 (13) 64 (9) H(16) (68) 3182 (21) 4849 (15) 75 (10) H(17) (84) 3978 (28) 3916 (21) 115 (15) H(18) 107 (68) 4641 (23) 3858 (16) 81 (11) H(19) 2693 (93) 4597 (30) 4634 (21) 133 (17) H(20) 1739 (64) 3810 (20) 5569 (16) 79 (10) H(211) (77) 2405 (24) 6662 (17) 83 (12) H(212) (70) 2672 (21) 6991 (13) 68 (10) H(22) (85) 3423 (28) 7133 (20) 93 (16) H(231) -287 (71) 9100 (24) 5238 (16) 85 (11) H(232) -445 (74) 8078 (25) 5085 (19) 93 (13) H(233) 1135 (99) 8384 (34) 5362 (24) 117 (21) H(241) -818 (69) 8936 (22) 6900 (17) 86 (12) H(242) 1919 (102) 8905 (33) 6434 (22) 139 (18) H(243) -435 (70) 9521 (25) 6264 (17) 92 (12) H(251) (93) 8303 (31) 6419 (24) 123 (18) H(252) (71) 8894 (25) 5823 (18) 89 (12) H(253) (68) 7928 (25) 5774 (18) 86 (12)

7 Anhang 184 Table 6: Torsion angles [deg]. C(25)-C(1)-C(2)-C(7) (4) C(24)-C(1)-C(2)-C(7) 57.8 (4) C(23)-C(1)-C(2)-C(7) (4) C(25)-C(1)-C(2)-C(3) 62.8 (4) C(24)-C(1)-C(2)-C(3) (3) C(23)-C(1)-C(2)-C(3) (4) C(7)-C(2)-C(3)-C(4) (3) C(1)-C(2)-C(3)-C(4) (2) C(2)-C(3)-C(4)-C(5) 54.6 (3) C(3)-C(4)-C(5)-O(8) (2) C(3)-C(4)-C(5)-C(6) (3) C(3)-C(4)-C(5)-C(12) 71.2 (3) O(8)-C(5)-C(6)-C(7) (3) C(12)-C(5)-C(6)-C(7) (4) C(4)-C(5)-C(6)-C(7) 57.8 (3) C(5)-C(6)-C(7)-C(2) (4) C(3)-C(2)-C(7)-C(6) 53.3 (4) C(1)-C(2)-C(7)-C(6) (3) C(6)-C(5)-O(8)-C(9) (2) C(12)-C(5)-O(8)-C(9) 43.4 (3) C(4)-C(5)-O(8)-C(9) (3) C(5)-O(8)-C(9)-O(90) (2) C(5)-O(8)-C(9)-N(10) -9.1 (3) O(90)-C(9)-N(10)-C(11) (2) O(8)-C(9)-N(10)-C(11) -9.9 (3) O(90)-C(9)-N(10)-C(13) -0.2 (4) O(8)-C(9)-N(10)-C(13) (2) C(9)-N(10)-C(11)-O(110) (2) C(13)-N(10)-C(11)-O(110) (4) C(9)-N(10)-C(11)-C(12) (3) C(13)-N(10)-C(11)-C(12) (2) O(110)-C(11)-C(12)-C(5) (3) N(10)-C(11)-C(12)-C(5) 44.6 (3) O(110)-C(11)-C(12)-C(120) 96.2 (3) N(10)-C(11)-C(12)-C(120) (3) O(8)-C(5)-C(12)-C(11) (3) C(6)-C(5)-C(12)-C(11) (2) C(4)-C(5)-C(12)-C(11) 61.6 (3) O(8)-C(5)-C(12)-C(120) 64.7 (3) C(6)-C(5)-C(12)-C(120) (4) C(4)-C(5)-C(12)-C(120) (3) C(9)-N(10)-C(13)-C(14) (3) C(11)-N(10)-C(13)-C(14) (3) C(9)-N(10)-C(13)-C(21) 67.9 (3) C(11)-N(10)-C(13)-C(21) (3)

8 Anhang 185 N(10)-C(13)-C(14)-C(15) (3) C(21)-C(13)-C(14)-C(15) (3) C(13)-C(14)-C(15)-C(20) 99.6 (3) C(13)-C(14)-C(15)-C(16) (4) C(20)-C(15)-C(16)-C(17) 1.0 (5) C(14)-C(15)-C(16)-C(17) (3) C(15)-C(16)-C(17)-C(18) -1.0 (6) C(16)-C(17)-C(18)-C(19) 0.2 (6) C(17)-C(18)-C(19)-C(20) 0.5 (6) C(16)-C(15)-C(20)-C(19) -0.3 (4) C(14)-C(15)-C(20)-C(19) (3) C(18)-C(19)-C(20)-C(15) -0.4 (5) N(10)-C(13)-C(21)-O(22) 42.9 (4) C(14)-C(13)-C(21)-O(22) (3)

9 Anhang Diastereomer B (Diplomarbeit) Table 1: Crystal data and structure refinement. Empirical formula: C 23 H 33 N O 4 Formula weight: Temperature: 20(2) C Wavelength: Å Crystal system: orthorhombic Space group: P Unit cell dimensions: a = 5.986(2) Å α = 90 deg. b = (3) Å β = 90 deg. c = (7) Å γ = 90 deg. Volume: (11) Å 3 Z: 4 Density (calculated): Mg/m 3 Absorption coefficient: 6.28 cm -1 F(000): 840 Crystal size: 0.70 x 0.10 x 0.05 mm 2 Θ range for data collection: 9.20 to deg. Index ranges: 08h85, 08k813, 08l829 Reflections collected: 1351 Independent reflections: 1351 [R int = ] Refinement method: Full-matrix least-squares on F 2 Data / restraints / parameters: 1351 / 0 / 256 Goodness-of-fit on F 2, S: Final R indices [I>2σ (I)]: R1 = , wr2 = 0,1270 R indices (all data): R1 = , wr2 = Absolute structure parameter: -0.9 (12) Extinction coefficient: (5) Largest diff. peak and hole: and e/å 3

10 Anhang 187 Table 2: Atomic coordinates ( ) and equivalent isotropic displacement parameters (Å ) U(eq) is defined as one third of the trace of the orthogonalized Uij tensor X Y Z U (eq) C(1) 5595 (23) 2896 (14) 1108 (5) 78 (5) C(2) 6116 (22) 3396 (11) 1584 (5) 57 (4) C(3) 7671 (21) 2734 (10) 1894 (4) 65 (4) C(4) 8446 (20) 3309 (10) 2332 (4) 73 (5) C(5) 6605 (22) 3753 (10) 2625 (4) 50 (4) C(6) 4928 (21) 4333 (8) 2322 (4) 60 (4) C(7) 4181 (21) 3676 (11) 1895 (5) 73 (4) O(8) 5232 (14) 2899 (7) 2825 (3) 66 (3) C(9) 5992 (29) 2457 (12) 3217 (6) 67 (5) O(90) 4899 (16) 1666 (7) 3356 (3) 74 (3) N(10) 7822 (21) 2777 (11) 3464 (4) 59 (4) C(11) 8653 (28) 3725 (16) 3376 (5) 74 (5) O(110) (21) 4014 (7) 3572 (3) 102 (4) C(12) 7281 (26) 4403 (10) 3039 (5) 72 (5) C(120) 8587 (24) 5363 (9) 2908 (4) 94 (6) C(13) 8835 (27) 2120 (11) 3829 (5) 73 (5) C(14) 7398 (23) 2032 (10) 4291 (4) 72 (5) C(15) 6642 (35) 3103 (12) 4469 (5) 66 (5) C(16) 4677 (34) 3484 (17) 4335 (6) 89 (6) C(17) 4129 (34) 4454 (18) 4529 (7) 104 (7) C(18) 5424 (46) 4928 (18) 4832 (7) 124 (9) C(19) 7402 (49) 4579 (16) 4968 (6) 116 (8) C(20) 8053 (28) 3590 (16) 4782 (5) 104 (7) C(21) 9395 (25) 1095 (11) 3651 (4) 78 (5) O(22) (18) 1082 (10) 3192 (3) 100 (4) C(23) 7705 (23) 2628 (12) 822 (4) 111 (6) C(24) 4016 (23) 3607 (11) 817 (4) 96 (6) C(25) 4296 (28) 1851 (12) 1175 (4) 103 (6)

11 Anhang 188 Table 3a: Bond lengths [Å]. C(1)-C(2) (14) N(10)-C(11) 1.36 (2) C(1)-C(24) 1.56 (2) N(10)-C(13) 1.47 (2) C(1)-C(23) 1.54 (2) C(11)-O(110) 1.24 (2) C(1)-C(25) 1.59 (2) C(11)-C(12) 1.54 (2) C(2)-C(7) 1.50 (2) C(12)-C(120) (14) C(2)-C(3) (14) C(13)-C(21) 1.48 (2) C(3)-C(4) (13) C(13)-C(14) 1.56 (2) C(4)-C(5) (14) C(14)-C(15) 1.56 (2) C(5)-O(8) (12) C(15)-C(16) 1.33 (2) C(5)-C(12) 1.50 (2) C(15)-C(20) 1.38 (2) C(5)-C(6) (13) C(16)-C(17) 1.42 (2) C(6)-C(7) (14) C(17)-C(18) 1.31 (2) O(8)-C(9) (14) C(18)-C(19) 1.33 (3) C(9)-O(90) (14) C(19)-C(20) 1.45 (2) C(9)-N(10) 1.36 (2) C(21)-O(22) (12) Table 3b: Bond angles [deg]. C(2)-C(1)-C(24) (12) C(11)-N(10)-C(9) (14) C(2)-C(1)-C(23) (12) C(11)-N(10)-C(13) (13) C(24)-C(1)-C(23) (13) C(9)-N(10)-C(13) (14) C(2)-C(1)-C(25) (12) O(110)-C(11)-N(10) 121 (2) C(24)-C(1)-C(25) (11) O(110)-C(11)-C(12) 123 (2) C(23)-C(1)-C(25) (13) N(10)-C(11)-C(12) 117 (2) C(7)-C(2)-C(1) (11) C(5)-C(12)-C(120) (12) C(7)-C(2)-C(3) (11) C(5)-C(12)-C(11) (12) C(1)-C(2)-C(3) (12) C(120)-C(12)-C(11) (14) C(4)-C(3)-C(2) (11) N(10)-C(13)-C(21) (12) C(5)-C(4)-C(3) (10) N(10)-C(13)-C(14) (12) C(4)-C(5)-O(8) (10) C(21)-C(13)-C(14) (12) C(4)-C(5)-C(12) (12) C(13)-C(14)-C(15) (11) O(8)-C(5)-C(12) (10) C(16)-C(15)-C(20) 123 (2) C(4)-C(5)-C(6) (10) C(16)-C(15)-C(14) 120 (2) O(8)-C(5)-C(6) (10) C(20)-C(15)-C(14) 117 (2) C(12)-C(5)-C(6) (12) C(15)-C(16)-C(17) 116 (2) C(5)-C(6)-C(7) (10) C(18)-C(17)-C(16) 123 (2) C(2)-C(7)-C(6) (10) C(17)-C(18)-C(19) 123 (2) C(9)-O(8)-C(5) (11) C(18)-C(19)-C(20) 116 (2) O(90)-C(9)-O(8) 116 (2) C(15)-C(20)-C(19) 119 (2) O(90)-C(9)-N(10) 120 (2) O(22)-C(21)-C(13) (12) O(8)-C(9)-N(10) (14)

12 Anhang 189 Table 4: Anisotropic displacement parameters (Å ). The anisotropic displacement factor exponent takes the form: - 2π 2 [h 2. a 2. U h. k. a. b. U 12 ] U11 U22 U33 U23 U13 U12 C(1) 40 (10) 113 (16) 80 (12) -16 (11) 0 (10) 1 (12) C(2) 65 (11) 59 (10) 48 (9) 4 (9) -21 (9) -11 (9) C(3) 67 (9) 87 (12) 41 (8) 2 (9) 33 (9) 5 (11) C(4) 61 (11) 84 (11) 75 (11) -14 (10) 17 (9) 14 (9) C(5) 54 (10) 56 (10) 38 (9) 17 (9) 1 (8) -17 (10) C(6) 71 (10) 39 (9) 69 (10) 5 (8) -5 (11) -23 (10) C(7) 56 (10) 87 (12) 76 (10) 18 (10) 6 (10) 14 (10) O(8) 80 (7) 67 (7) 51 (6) 7 (5) 3 (6) -7 (7) C(9) 73 (13) 77 (14) 50 (11) 25 (10) 51 (10) -1 (12) O(90) 85 (8) 78 (7) 58 (6) -4 (6) -6 (5) -3 (7) N(10) 44 (8) 65 (11) 66 (9) -4 (8) -21 (7) -17 (8) C(11) 73 (14) 103 (17) 47 (10) -37 (11) 23 (9) -35 (14) O(110) 134 (9) 67 (8) 105 (8) 5 (6) -41 (9) -41 (8) C(12) 97 (12) 54 (12) 65 (11) -12 (9) -5 (11) 33 (11) C(120) 148 (16) 35 (10) 100 (11) -5 (8) 13 (11) -38 (11) C(13) 102 (12) 39 (11) 78 (11) -5 (10) 2 (11) 19 (10) C(14) 80 (11) 88 (14) 50 (9) 14 (9) 8 (9) -7 (11) C(15) 87 (14) 74 (14) 37 (9) 3 (9) 17 (10) 8 (13) C(16) 70 (14) 106 (18) 91 (14) 5 (13) -11 (12) -1 (14) C(17) 100 (18) 138 (21) 73 (14) 37 (15) -6 (14) 4 (17) C(18) 145 (23) 150 (22) 76 (16) 28 (15) -39 (15) 9 (19) C(19) 190 (27) 86 (17) 72 (13) -25 (12) -44 (15) -49 (19) C(20) 115 (14) 158 (20) 39 (10) 2 (11) -22 (11) -99 (16) C(21) 83 (11) 79 (13) 71 (11) 10 (10) 20 (10) -2 (12) O(22) 61 (8) 144 (10) 95 (8) -9 (7) -7 (7) 2 (9) C(23) 79 (11) 177 (17) 77 (11) -40 (11) 13 (11) -4 (15) C(24) 89 (13) 137 (14) 62 (10) 11 (11) -19 (10) -21 (13) C(25) 113 (14) 120 (14) 75 (11) -28 (10) 6 (11) -29 (15)

13 Anhang 190 Table 5: Hydrogen coordinates ( ) and isotropic displacement parameters (Å ). X Y Z U H(2) 6925 (22) 4027 (11) 1515 (5) 69 H(3A) 6883 (21) 2124 (10) 1991 (4) 78 H(3B) 8961 (21) 2530 (10) 1709 (4) 78 H(4A) 9309 (20) 2849 (10) 2530 (4) 88 H(4B) 9432 (20) 3855 (10) 2233 (4) 88 H(6A) 5603 (21) 4958 (8) 2208 (4) 72 H(6B) 3638 (21) 4511 (8) 2513 (4) 72 H(7A) 3471 (21) 3060 (11) 2011 (5) 88 H(7B) 3090 (21) 4050 (11) 1710 (5) 88 H(12) 5920 (26) 4613 (10) 3206 (5) 86 H(12A) 9790 (24) 5457 (9) 3129 (4) 141 H(12B) 7609 (24) 5941 (9) 2919 (4) 141 H(12C) 9182 (24) 5292 (9) 2593 (4) 141 H(13) (27) 2442 (11) 3921 (5) 87 H(14A) 8267 (23) 1699 (10) 4537 (4) 87 H(14B) 6092 (23) 1616 (10) 4228 (4) 87 H(16) 3728 (34) 3140 (17) 4129 (6) 107 H(17) 2800 (34) 4762 (18) 4437 (7) 125 H(18) 4929 (46) 5541 (18) 4959 (7) 148 H(19) 8324 (49) 4947 (16) 5170 (6) 139 H(20) 9395 (28) 3292 (16) 4873 (5) 125 H(21A) (25) 776 (11) 3871 (4) 93 H(21B) 8044 (25) 688 (11) 3645 (4) 93 H(22) (26) 1132 (95) 3215 (4) 56 (47) H(23A) 8000 (23) 3157 (12) 596 (4) 167 H(23B) 7478 (23) 1996 (12) 658 (4) 167 H(23C) 8953 (23) 2564 (12) 1034 (4) 167 H(24A) 2669 (23) 3247 (11) 740 (4) 144 H(24B) 4753 (23) 3814 (11) 531 (4) 144 H(24C) 3656 (23) 4197 (11) 1003 (4) 144 H(25A) 4658 (28) 1400 (12) 918 (4) 154 H(25B) 2716 (28) 1978 (12) 1177 (4) 154 H(25C) 4728 (28) 1545 (12) 1471 (4) 154

14 Anhang 191 Table 6: Torsion angles [deg]. C(24)-C(1)-C(2)-C(7) 57 (2) C(23)-C(1)-C(2)-C(7) (14) C(25)-C(1)-C(2)-C(7) -61 (2) C(24)-C(1)-C(2)-C(3) (10) C(23)-C(1)-C(2)-C(3) -56 (2) C(25)-C(1)-C(2)-C(3) 62.5 (14) C(7)-C(2)-C(3)-C(4) (13) C(1)-C(2)-C(3)-C(4) (11) C(2)-C(3)-C(4)-C(5) 54 (2) C(3)-C(4)-C(5)-O(8) 64.8 (14) C(3)-C(4)-C(5)-C(12) (11) C(3)-C(4)-C(5)-C(6) -48 (2) C(4)-C(5)-C(6)-C(7) 49.7 (14) O(8)-C(5)-C(6)-C(7) (12) C(12)-C(5)-C(6)-C(7) (11) C(1)-C(2)-C(7)-C(6) (11) C(3)-C(2)-C(7)-C(6) 63.4 (14) C(5)-C(6)-C(7)-C(2) (13) C(4)-C(5)-O(8)-C(9) 82.7 (12) C(12)-C(5)-O(8)-C(9) (13) C(6)-C(5)-O(8)-C(9) (10) C(5)-O(8)-C(9)-O(90) (10) C(5)-O(8)-C(9)-N(10) 5 (2) O(90)-C(9)-N(10)-C(11) (12) O(8)-C(9)-N(10)-C(11) 16 (2) O(90)-C(9)-N(10)-C(13) 12 (2) O(8)-C(9)-N(10)-C(13) (12) C(9)-N(10)-C(11)-O(110) (12) C(13)-N(10)-C(11)-O(110) 7 (2) C(9)-N(10)-C(11)-C(12) 6 (2) C(13)-N(10)-C(11)-C(12) (11) C(4)-C(5)-C(12)-C(120) 62 (2) O(8)-C(5)-C(12)-C(120) (10) C(6)-C(5)-C(12)-C(120) (14) C(4)-C(5)-C(12)-C(11) -61 (2) O(8)-C(5)-C(12)-C(11) 60.2 (13) C(6)-C(5)-C(12)-C(11) (11) O(110)-C(11)-C(12)-C(5) (14) N(10)-C(11)-C(12)-C(5) -45 (2) O(110)-C(11)-C(12)-C(120) 11 (2) N(10)-C(11)-C(12)-C(120) (11) C(11)-N(10)-C(13)-C(21) (14) C(9)-N(10)-C(13)-C(21) 54 (2) C(11)-N(10)-C(13)-C(14) (14) C(9)-N(10)-C(13)-C(14) (14)

15 Anhang 192 N(10)-C(13)-C(14)-C(15) -49 (2) C(21)-C(13)-C(14)-C(15) (14) C(13)-C(14)-C(15)-C(16) 93 (2) C(13)-C(14)-C(15)-C(20) -90 (2) C(20)-C(15)-C(16)-C(17) 1 (2) C(14)-C(15)-C(16)-C(17) (12) C(15)-C(16)-C(17)-C(18) -2 (3) C(16)-C(17)-C(18)-C(19) 4 (3) C(17)-C(18)-C(19)-C(20) -3 (3) C(16)-C(15)-C(20)-C(19) -2 (2) C(14)-C(15)-C(20)-C(19) (14) C(18)-C(19)-C(20)-C(15) 2 (3) N(10)-C(13)-C(21)-O(22) 42 (2) C(14)-C(13)-C(21)-O(22) (11)

16 Anhang Aldoladdukt 5A Table 1: Crystal data and structure refinement. Empirical formula: C 24 H 36 N 2 O 3 Formula weight: Temperature: -140 C Radiation: Mo-K α Crystal system: orthorhombic Space group: P Unit cell dimensions: a = 6.296(1) Å α = 90 deg. b = (2) Å β = 90 deg. c = 35.58(1) Å γ = 90 deg. Volume: (9) Å 3 Z: 4 Density (calculated): g/cm 3 Absorption coefficient: 0.7 cm -1 Crystal color: colorless, transparent Crystal size: 0.04 x 0.15 x 1.20 mm Scan range: sphere (2 Θ)max: 52 deg. Resolution: 0.80 Å Reflections collected: Independent reflections: 2596 Reflections used with I > 0: 2510 Number of variables: 407 R (F): wr (F): S: 0.76

17 Anhang 194 Table 2: Atomic coordinates and equivalent isotropic displacement parameters (Å 2 ). Starred atoms were refined isotropically. Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3). [a 2. B(1,1) + b 2. B(2,2) + c 2. B(3,3) + a. b. (cos γ). B(1,2) + a. c. (cos β). B(1,3) + b. c. (cos α). B(2,3)] X Y Z U (eq) O (4) (2) (5) 1.97 (5) O (4) (2) (6) 2.69 (5) O (4) (2) (6) 2.55 (5) N (4) (2) (7) 1.71 (5) N (4) (2) (7) 1.75 (6) C (5) (3) (8) 1.93 (7) C (5) (3) (8) 1.79 (7) C (6) (3) (8) 1.97 (7) C (6) (3) (8) 1.95 (7) C (6) (3) (9) 1.98 (7) C (6) (3) (9) 2.00 (7) C (6) (3) (9) 2.18 (8) C (6) (3) (9) 2.40 (8) C (6) (3) (9) 2.46 (8) C (6) (3) (9) 2.50 (8) C (6) (3) (1) 2.41 (8) C (6) (3) (9) 2.38 (8) C (6) (3) (9) 2.65 (8) C (6) (3) (8) 1.80 (7) C (6) (4) (9) 2.84 (8) C (7) (4) (1) 4.4 (1) C (7) (4) (9) 3.9 (1) C (6) (4) (9) 3.32 (9) C (6) (4) (9) 2.76 (8) C (7) (3) (9) 3.05 (9) C (6) (3) (9) 2.81 (9) C (8) (4) (1) 4.2 (1) C (7) (4) (1) 3.9 (1) C (8) (4) (9) 4.7 (1)

18 Anhang 195 Table 3a: Bond lengths [Å]. Numbers in parentheses are estimated standard deviations in the least significant digits. O1-C (4) C6-C (5) O2-C (4) C7-C (5) O3-C (4) C8-C (5) N1-C (4) C9-C (5) N1-C (4) C9-C (5) N1-C (4) C10-C (5) N2-C (4) C14-C (5) N2-C (4) C14-C (5) N2-C (4) C15-C (5) C2-C (4) C16-C (6) C2-C (5) C17-C (6) C3-C (4) C18-C (5) C4-C (5) C21-C (6) C5-C (4) C21-C (6) C5-C (5) C21-C (5) C6-C (5) Table 3b: Bond angles [deg]. C1-N1-C (2) C5-C6-C (3) C1-N1-C (3) C5-C6-C (3) C3-N1-C (3) C7-C6-C (3) C1-N2-C (3) C6-C7-C (3) C1-N2-C (3) C7-C8-C (3) C2-N2-C (3) C8-C9-C (3) O1-C1-N (3) C8-C9-C (3) O1-C1-N (3) C10-C9-C (3) N1-C1-N (3) C9-C10-C (3) N2-C2-C (3) C6-C11-C (3) N2-C2-C (3) C3-C14-C (3) C3-C2-C (3) C3-C14-C (3) N1-C3-C (3) C15-C14-C (3) N1-C3-C (3) C14-C15-C (3) C2-C3-C (3) C15-C16-C (4) O2-C4-N (3) C16-C17-C (3) O2-C4-C (3) C17-C18-C (3) N1-C4-C (3) C14-C19-C (3) C4-C5-C (3) C9-C21-C (3) C4-C5-C (3) C9-C21-C (3) C6-C5-C (3) C9-C21-C (3) O3-C6-C (3) C22-C21-C (3) O3-C6-C (3) C22-C21-C (3) O3-C6-C (3) C23-C21-C (3)

19 Anhang 196 Table 4: Anisotropic displacement parameters (Å 2 ). The form of the anisotropic displacement parameter is: exp [ -2π 2. ( h 2. a 2. U 11 + k 2. b 2. U 22 + l 2. c 2. U h. k. a. b. U h. l. a. c. U k. l. b. c. U 23 )] where a, b, and c are reciprocal lattice constants. U11 U22 U33 U23 U13 U12 O (1) (1) (1) (1) (1) (1) O (1) (1) (1) (1) (1) (1) O (1) (1) (1) (1) (1) (1) N (2) (1) (1) (2) (1) (1) N (2) (1) (1) (2) (1) (1) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (3) (3) (2) (3) (2) (2) C (3) (3) (2) (3) (2) (2) C (2) (3) (2) (3) (2) (2) C (2) (2) (2) (2) (2) (2) C (3) (2) (2) (2) (2) (2) C (2) (2) (2) (2) (2) (2) C (3) (3) (2) (3) (3) (2) C (3) (3) (2) (3) (2) (2) C (3) (3) (2) (3) (2) (2)

20 Anhang 197 Table 5: Hydrogen coordinates ( ) and isotropic displacement parameters (Å ). Starred atoms were refined isotropically. Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3). [a 2. B(1,1) + b 2. B(2,2) + c 2. B(3,3) + a. b. (cos γ). B(1,2) + a. c. (cos β). B(1,3) + b. c. (cos α). B(2,3)] X Y Z U H (5) (2) (6) 2.3 (7)* H (4) (2) (5) -0.8 (5)* H (5) (2) (7) 2.5 (7)* H7a (4) (3) (7) 2.2 (7)* H7b (5) (3) (7) 3.0 (7)* H8a (5) (3) (7) 2.6 (7)* H8b (5) (3) (8) 4.3 (8)* H (4) (2) (6) 1.0 (6)* H10a (4) (2) (5) -0.2 (5)* H10b (4) (2) (6) 0.9 (6)* H11a (4) (2) (6) 0.9 (6)* H11b (5) (3) (8) 3.8 (8)* H (5) (3) (7) 2.7 (7)* H (5) (3) (7) 2.5 (7)* H (5) (3) (7) 2.4 (7)* H (5) (3) (8) 4.1 (8)* H (4) (2) (5) -0.6 (5)* H20a (4) (2) (6) 2.2 (7)* H20b (6) (3) (9) 7 (1)* H20c (5) (2) (7) 1.9 (7)* H22a (5) (3) (7) 3.2 (8)* H22b (5) (3) (7) 3.1 (8)* H22c (7) (4) (1) 8 (1)* H23a (6) (3) (9) 6 (1)* H23b (7) (4) (1) 8 (1)* H23c (5) (3) (7) 2.5 (7)* H24a (6) (3) (8) 4.5 (8)* H24b (6) (3) (9) 6 (1)* H24c (6) (4) (9) 7 (1)* H (6) (3) (9) 6 (1)* H12a (5) (3) (8) 3.4 (8)* H12b (4) (2) (6) 1.3 (6)* H13a (6) (3) (8) 4.6 (9)* H13b (5) (2) (7) 2.6 (7)* H12c (5) (3) (7) 3.8 (8)* H13c (5) (3) (8) 4.9 (9)*

21 Anhang 198 Table 6: Torsion angles [deg]. C3-N1-C1-O (0.28) C3-N1-C1-N (0.32) C4-N1-C1-O (0.49) C4-N1-C1-N (0.27) C1-N1-C3-C (0.30) C1-N1-C3-C (0.29) C4-N1-C3-C (0.25) C4-N1-C3-C (0.35) C1-N1-C4-O (0.28) C1-N1-C4-C (0.44) C3-N1-C4-O (0.40) C3-N1-C4-C (0.26) C2-N2-C1-O (0.29) C2-N2-C1-N (0.32) C12-N2-C1-O (0.47) C12-N2-C1-N (0.25) C1-N2-C2-C (0.30) C1-N2-C2-C (0.26) C12-N2-C2-C (0.25) C12-N2-C2-C (0.35) N2-C2-C3-N (0.28) N2-C2-C3-C (0.31) C13-C2-C3-N (0.28) C13-C2-C3-C (0.43) N1-C3-C14-C (0.33) N1-C3-C14-C (0.42) C2-C3-C14-C (0.36) C2-C3-C14-C (0.43) O2-C4-C5-C (0.39) O2-C4-C5-C (0.36) N1-C4-C5-C (0.28) N1-C4-C5-C (0.32) C4-C5-C6-O (0.32) C4-C5-C6-C (0.26) C4-C5-C6-C (0.36) C20-C5-C6-O (0.38) C20-C5-C6-C (0.37) C20-C5-C6-C (0.30) O3-C6-C7-C (0.32) C5-C6-C7-C (0.26) C11-C6-C7-C (0.35) O3-C6-C11-C (0.36) C5-C6-C11-C (0.29) C7-C6-C11-C (0.37)

22 Anhang 199 C6-C7-C8-C (0.39) C7-C8-C9-C (0.39) C7-C8-C9-C (0.30) C8-C9-C10-C (0.37) C21-C9-C10-C (0.28) C8-C9-C21-C (0.41) C8-C9-C21-C (0.39) C8-C9-C21-C (0.32) C10-C9-C21-C (0.39) C10-C9-C21-C (0.29) C10-C9-C21-C (0.42) C9-C10-C11-C (0.39) C3-C14-C15-C (0.35) C19-C14-C15-C (0.54) C3-C14-C19-C (0.66) C15-C14-C19-C (0.55) C14-C15-C16-C (0.64) C15-C16-C17-C (0.67) C16-C17-C18-C (0.64) C17-C18-C19-C (0.62)

23 Anhang Aldoladdukt 13A Table 1: Crystal data and structure refinement. Empirical formula: C 35 H 60 N 2 O 5 Si 2 Formula weight: Temperature: -139 C Radiation: Mo-K α Crystal system: orthorhombic Space group: P Unit cell dimensions: a = (9) Å α = 90 deg. b = (2) Å β = 90 deg. c = (9) Å γ = 90 deg. Volume: 3703(1) Å 3 Z: 4 Density (calculated): g/cm 3 Absorption coefficient: 1.31 cm -1 Crystal color: colorless, transparent Crystal size: 0.04 x 0.12 x 0.84 mm Scan range: sphere (2 Θ)max: 49 deg. Resolution: 0.86 Å Reflections collected: Independent reflections: 5540 Reflections used with I > 0: 5516 Number of variables: 637 R (F): wr (F): S: 1.10

24 Anhang 201 Table 2: Atomic coordinates and equivalent isotropic displacement parameters (Å 2 ). Starred atoms were refined isotropically. Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3). [a 2. B(1,1) + b 2. B(2,2) + c 2. B(3,3) + a. b. (cos γ). B(1,2) + a. c. (cos β). B(1,3) + b. c. (cos α). B(2,3)] X Y Z U (eq) SI (2) (2) (2) 2.30 (3) SI (2) (1) (2) 1.61 (3) O (5) (3) (5) 1.82 (7) O (5) (4) (5) 2.20 (7) O (5) (3) (5) 1.82 (7) O (5) (3) (5) 1.87 (7) O (5) (3) (5) 2.33 (7) N (6) (4) (6) 1.81 (9) N (6) (4) (6) 1.19 (8) C (7) (5) (7) 1.6 (1) C (7) (5) (8) 1.7 (1) C (7) (5) (8) 1.7 (1) C (7) (5) (7) 1.6 (1) C (7) (5) (8) 1.4 (1) C (7) (5) (7) 1.4 (1) C (7) (5) (7) 1.4 (1) C (7) (5) (7) 1.6 (1) C (7) (5) (8) 2.0 (1) C (7) (5) (7) 1.4 (1) C (7) (5) (7) 1.3 (1) C (8) (5) (8) 1.6 (1) C (7) (5) (7) 1.4 (1) C (8) (6) (8) 3.1 (1) C (8) (6) (8) 2.5 (1) C (7) (5) (7) 1.5 (1) C (7) (5) (8) 2.2 (1) C (8) (6) (9) 3.3 (1) C (9) (5) (8) 2.8 (1) C (8) (5) (9) 2.7 (1) C (8) (5) (8) 1.8 (1) C (8) (5) (8) 2.4 (1) C (8) (5) (8) 2.6 (1) C (9) (6) (1) 3.9 (1) C (8) (5) (8) 2.5 (1) C (9) (6) (8) 3.5 (1) C (9) (6) (9) 3.6 (1) C (8) (6) (8) 3.0 (1)

25 Anhang 202 C (8) (5) (8) 1.9 (1) C (8) (6) (8) 2.6 (1) C (8) (6) (8) 2.7 (1) C (7) (5) (8) 1.6 (1) C (1) (5) (8) 3.3 (1) C (9) (5) (8) 3.4 (1) C (9) (6) (8) 3.0 (1)

26 Anhang 203 Table 3a: Bond lengths [Å]. Numbers in parentheses are estimated standard deviations in the least significant digits. SI1-O (3) C5-C (7) SI1-C (6) C6-C (6) SI1-C (6) C6-C (7) SI1-C (5) C7-C (6) SI2-O (4) C8-C (6) SI2-C (5) C8-C (7) SI2-C (5) C9-C (6) SI2-C (5) C10-C (6) O1-C (6) C11-C (6) O2-C (5) C11-C (7) O3-C (5) C12-C (6) O4-C (5) C16-C (7) O5-C (6) C16-C (7) N1-C (6) C17-C (7) N1-C (6) C18-C (8) N1-C (6) C19-C (8) N2-C (6) C20-C (7) N2-C (6) C25-C (7) N2-C (5) C25-C (8) C2-C (6) C25-C (8) C2-C (7) C32-C (7) C3-C (7) C32-C (7) C4-C (6) C32-C (8) C5-C (6)

27 Anhang 204 Table 3b: Bond angles [deg]. O4-SI1-C (2) C5-C6-C (4) O4-SI1-C (2) C7-C6-C (4) O4-SI1-C (2) C6-C7-C (4) C23-SI1-C (2) C7-C8-C (4) C23-SI1-C (2) C7-C8-C (4) C24-SI1-C (2) C9-C8-C (3) O5-SI2-C (2) C8-C9-C (4) O5-SI2-C (2) O4-C10-C (4) O5-SI2-C (2) O4-C10-C (4) C30-SI2-C (2) C9-C10-C (3) C30-SI2-C (2) C10-C11-C (4) C31-SI2-C (2) C10-C11-C (4) SI1-O4-C (3) C12-C11-C (4) SI2-O5-C (3) C8-C12-C (4) C1-N1-C (4) C8-C12-C (4) C1-N1-C (4) C11-C12-C (4) C2-N1-C (4) C6-C13-C (4) C1-N2-C (3) C3-C16-C (4) C1-N2-C (4) C3-C16-C (4) C3-N2-C (3) C17-C16-C (4) O1-C1-N (4) C16-C17-C (5) O1-C1-N (4) C17-C18-C (5) N1-C1-N (4) C18-C19-C (5) N1-C2-C (3) C19-C20-C (5) N1-C2-C (4) C16-C21-C (4) C3-C2-C (4) SI1-C25-C (4) N2-C3-C (3) SI1-C25-C (3) N2-C3-C (4) SI1-C25-C (3) C2-C3-C (4) C26-C25-C (4) O2-C4-N (4) C26-C25-C (4) O2-C4-C (4) C27-C25-C (4) N2-C4-C (4) O5-C29-C (4) C4-C5-C (4) SI2-C32-C (3) C4-C5-C (4) SI2-C32-C (3) C6-C5-C (4) SI2-C32-C (3) O3-C6-C (4) C33-C32-C (4) O3-C6-C (3) C33-C32-C (4) O3-C6-C (3) C34-C32-C (4) C5-C6-C (4)

28 Anhang 205 Table 4: Anisotropic displacement parameters (Å 2 ). The form of the anisotropic displacement parameter is: exp [ -2π 2. ( h 2. a 2. U 11 + k 2. b 2. U 22 + l 2. c 2. U h. k. a. b. U h. l. a. c. U k. l. b. c. U 23 )] where a, b, and c are reciprocal lattice constants. U11 U22 U33 U23 U13 U12 SI (8) (8) (6) (8) (7) (7) SI (7) (7) (6) (7) (6) (7) O (2) (2) (2) (2) (2) (2) O (2) (2) (2) (2) (2) (2) O (2) (2) (2) (2) (2) (2) O (2) (2) (2) (2) (2) (2) O (2) (2) (2) (2) (2) (2) N (2) (2) (2) (2) (2) (2) N (2) (2) (2) (2) (2) (2) C (3) (3) (2) (2) (2) (2) C (3) (3) (2) (3) (2) (2) C (2) (3) (2) (2) (2) (2) C (3) (3) (2) (3) (2) (2) C (3) (2) (2) (2) (2) (2) C (3) (3) (2) (3) (2) (2) C (3) (3) (2) (2) (2) (2) C (3) (3) (2) (2) (2) (2) C (3) (3) (2) (3) (3) (2) C (3) (2) (2) (2) (2) (2) C (3) (3) (2) (2) (2) (2) C (3) (3) (2) (2) (2) (2) C (2) (3) (2) (3) (2) (2) C (3) (4) (3) (3) (3) (3) C (3) (3) (3) (3) (3) (3) C (3) (3) (2) (2) (2) (2) C (3) (3) (3) (3) (2) (3) C (3) (4) (3) (3) (3) (3) C (4) (3) (2) (3) (3) (2) C (3) (3) (3) (3) (3) (3) C (3) (3) (2) (3) (2) (2) C (3) (3) (3) (3) (3) (3) C (3) (3) (3) (3) (3) (3) C (3) (4) (4) (3) (3) (4) C (3) (3) (3) (3) (3) (3) C (4) (4) (3) (4) (3) (3) C (4) (4) (3) (3) (3) (3) C (3) (4) (3) (3) (3) (3) C (3) (3) (2) (3) (2) (2)

29 Anhang 206 C (3) (3) (3) (3) (2) (3) C (3) (4) (3) (3) (3) (3) C (3) (3) (2) (2) (2) (2) C (4) (3) (2) (4) (3) (3) C (4) (3) (3) (4) (3) (3) C (4) (3) (3) (3) (3) (3)

30 Anhang 207 Table 5: Hydrogen coordinates ( ) and isotropic displacement parameters (Å ). Starred atoms were refined isotropically. Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3). [a 2. B(1,1) + b 2. B(2,2) + c 2. B(3,3) + a. b. (cos γ). B(1,2) + a. c. (cos β). B(1,3) + b. c. (cos α). B(2,3)] X Y Z U H (5) (3) (5) -0.6 (7)* H (5) (3) (5) 0.3 (8)* H (5) (3) (6) 0.5 (8)* H (5) (3) (5) -0.3 (7)* H7A (5) (3) (5) 0.1 (8)* H7B (6) (4) (7) 3 (1)* H (5) (3) (5) -0.5 (7)* H9B (7) (5) (7) 4 (1)* H9A (5) (3) (5) 0.0 (7)* H (5) (3) (6) 0.7 (8)* H (5) (3) (5) 0.1 (8)* H (5) (3) (5) -0.2 (7)* H13A (5) (4) (5) 0.3 (8)* H13B (5) (3) (5) -0.6 (7)* H14A (6) (4) (6) 2 (1)* H14B (7) (5) (8) 5 (1)* H14C (5) (4) (6) 0.8 (8)* H15C (5) (3) (5) -0.0 (7)* H15A (5) (4) (6) 1.4 (9)* H15B (7) (4) (8) 4 (1)* H (5) (3) (5) 0.3 (8)* H (6) (4) (6) 2 (1)* H (5) (3) (5) -0.4 (7)* H (5) (4) (6) 0.9 (8)* H (6) (4) (6) 2 (1)* H22A (6) (4) (6) 1.3 (9)* H22C (8) (5) (8) 6 (1)* H22B (4) (3) (5) -1.0 (7)* H23C (7) (4) (7) 3 (1)* H23A (8) (6) (9) 7 (2)* H23B (1) (7) (1) 13 (2)* H24B (8) (6) (9) 8 (2)* H24C (6) (4) (7) 3 (1)* H24A (6) (4) (7) 3 (1)* H26B (5) (3) (5) 0.2 (8)* H26A (9) (5) (8) 7 (2)* H26C (7) (5) (7) 4 (1)*

31 Anhang 208 H27C (6) (4) (6) 2 (1)* H27B (9) (5) (8) 6 (1)* H27A (6) (4) (6) 2 (1)* H28B (5) (4) (6) 0.6 (8)* H28A (5) (3) (5) -0.4 (7)* H28C (8) (6) (9) 7 (2)* H29A (5) (4) (6) 0.8 (8)* H29B (6) (4) (5) 0.7 (8)* H30B (7) (5) (7) 4 (1)* H30C (7) (5) (7) 4 (1)* H30A (7) (6) (9) 6 (2)* H31A (5) (3) (5) -0.1 (8)* H31C (6) (4) (7) 3 (1)* H31B (7) (5) (7) 4 (1)* H33A (6) (4) (7) 3 (1)* H33C (5) (4) (6) 0.9 (9)* H33B (8) (5) (8) 6 (1)* H34C (5) (4) (6) 1.1 (9)* H34B (7) (4) (7) 4 (1)* H34A (7) (5) (8) 6 (1)* H35A (5) (3) (5) -0.2 (8)* H35C (6) (4) (6) 1 (1)* H35B (8) (5) (8) 5 (1)*

32 Anhang 209 Table 6: Torsion angles [deg]. C23-SI1-O4-C (0.39) C24-SI1-O4-C (0.38) C25-SI1-O4-C (0.34) O4-SI1-C25-C (0.37) O4-SI1-C25-C (0.39) O4-SI1-C25-C (0.38) C23-SI1-C25-C (0.44) C23-SI1-C25-C (0.41) C23-SI1-C25-C (0.33) C24-SI1-C25-C (0.45) C24-SI1-C25-C (0.36) C24-SI1-C25-C (0.40) C30-SI2-O5-C (0.40) C31-SI2-O5-C (0.37) C32-SI2-O5-C (0.35) O5-SI2-C32-C (0.38) O5-SI2-C32-C (0.33) O5-SI2-C32-C (0.36) C30-SI2-C32-C (0.41) C30-SI2-C32-C (0.40) C30-SI2-C32-C (0.33) C31-SI2-C32-C (0.35) C31-SI2-C32-C (0.40) C31-SI2-C32-C (0.39) SI1-O4-C10-C (0.44) SI1-O4-C10-C (0.30) SI2-O5-C29-C (0.33) C2-N1-C1-O (0.45) C2-N1-C1-N (0.50) C14-N1-C1-O (0.73) C14-N1-C1-N (0.40) C1-N1-C2-C (0.49) C1-N1-C2-C (0.40) C14-N1-C2-C (0.42) C14-N1-C2-C (0.56) C3-N2-C1-O (0.45) C3-N2-C1-N (0.49) C4-N2-C1-O (0.76) C4-N2-C1-N (0.41) C1-N2-C3-C (0.47) C1-N2-C3-C (0.40) C4-N2-C3-C (0.37) C4-N2-C3-C (0.51) C1-N2-C4-O (0.42)

33 Anhang 210 C1-N2-C4-C (0.68) C3-N2-C4-O (0.61) C3-N2-C4-C (0.40) N1-C2-C3-N (0.43) N1-C2-C3-C (0.44) C15-C2-C3-N (0.40) C15-C2-C3-C (0.59) N2-C3-C16-C (0.43) N2-C3-C16-C (0.56) C2-C3-C16-C (0.49) C2-C3-C16-C (0.57) O2-C4-C5-C (0.61) O2-C4-C5-C (0.53) N2-C4-C5-C (0.42) N2-C4-C5-C (0.47) C4-C5-C6-O (0.47) C4-C5-C6-C (0.38) C4-C5-C6-C (0.50) C22-C5-C6-O (0.50) C22-C5-C6-C (0.50) C22-C5-C6-C (0.39) O3-C6-C7-C (0.39) C5-C6-C7-C (0.38) C13-C6-C7-C (0.44) O3-C6-C13-C (0.42) C5-C6-C13-C (0.38) C7-C6-C13-C (0.43) C6-C7-C8-C (0.42) C6-C7-C8-C (0.45) C7-C8-C9-C (0.41) C12-C8-C9-C (0.47) C7-C8-C12-C (0.38) C7-C8-C12-C (0.45) C9-C8-C12-C (0.46) C9-C8-C12-C (0.37) C8-C9-C10-O (0.36) C8-C9-C10-C (0.44) O4-C10-C11-C (0.35) O4-C10-C11-C (0.50) C9-C10-C11-C (0.42) C9-C10-C11-C (0.38) C10-C11-C12-C (0.42) C10-C11-C12-C (0.40) C29-C11-C12-C (0.39) C29-C11-C12-C (0.54) C10-C11-C29-O (0.48) C12-C11-C29-O (0.51)

34 Anhang 211 C8-C12-C13-C (0.45) C11-C12-C13-C (0.47) C3-C16-C17-C (0.44) C21-C16-C17-C (0.71) C3-C16-C21-C (0.43) C17-C16-C21-C (0.67) C16-C17-C18-C (0.75) C17-C18-C19-C (0.76) C18-C19-C20-C (0.75) C19-C20-C21-C (0.73)

35 Anhang Aldoladdukt 13B Table 1: Crystal data and structure refinement. Empirical formula: C 35 H 60 N 2 O 5 Si 2 Formula weight: Temperature: -139 C Radiation: Mo-K α Crystal system: monoclinic Space group: P21 Unit cell dimensions: a = (7) Å α = 90 deg. b = (2) Å β = 95.73(1) deg. c = (3) Å γ = 90 deg. Volume: (5) Å 3 Z: 2 Density (calculated): g/cm 3 Absorption coefficient: 1.3 cm -1 Crystal color: colorless, transparent Crystal size: 0.05 x 0.40 x 0.80 mm Scan range: sphere (2 Θ)max: 61 deg. Resolution: 0.70 Å Reflections collected: Independent reflections: 9274 Reflections used with I > 0: 9058 Number of variables: 637 R (F): wr (F): S: 1.17

36 Anhang 213 Table 2: Atomic coordinates and equivalent isotropic displacement parameters (Å 2 ). Starred atoms were refined isotropically. Anisotropically refined atoms are given in the form of the isotropic equivalent displacement parameter defined as: (4/3). [a 2. B(1,1) + b 2. B(2,2) + c 2. B(3,3) + a. b. (cos γ). B(1,2) + a. c. (cos β). B(1,3) + b. c. (cos α). B(2,3)] X Y Z U (eq) Si (8) (0) (2) (9) Si (8) (5) (2) (9) O (2) (1) (6) 1.77 (2) O (2) (1) (6) 1.90 (3) O (2) (1) (5) 1.66 (2) O (2) (1) (5) 1.86 (3) O (2) (1) (6) 2.13 (3) N (2) (1) (6) 1.48 (3) N (2) (1) (6) 1.26 (3) C (3) (1) (8) 1.37 (3) C (3) (2) (8) 1.60 (3) C (3) (2) (7) 1.41 (3) C (3) (1) (8) 1.32 (3) C (3) (1) (7) 1.28 (3) C (3) (1) (7) 1.19 (3) C (3) (2) (8) 1.42 (3) C (3) (2) (8) 1.42 (3) C (3) (2) (8) 1.91 (4) C (3) (2) (8) 1.68 (4) C (3) (2) (8) 1.50 (3) C (3) (1) (7) 1.38 (3) C (3) (2) (8) 1.38 (3) C (3) (2) (8) 1.92 (4) C (3) (2) (8) 2.24 (4) C (3) (2) (8) 1.50 (3) C (3) (2) (9) 2.13 (4) C (4) (2) (9) 2.90 (4) C (4) (2) (9) 2.89 (5) C (4) (2) (9) 2.37 (4) C (3) (2) (8) 1.79 (4) C (3) (2) (8) 1.69 (4) C (4) (2) (1) 2.86 (5) C (3) (2) (9) 2.50 (4) C (3) (2) (8) 2.11 (4) C (4) (2) (1) 3.70 (5) C (4) (2) (1) 3.58 (5) C (4) (2) (9) 3.00 (5)

37 Anhang 214 C (3) (2) (8) 2.12 (4) C (4) (2) (9) 2.59 (4) C (4) (2) (1) 2.95 (5) C (3) (2) (8) 1.90 (4) C (4) (2) (1) 3.06 (5) C (4) (2) (1) 2.83 (5) C (4) (2) (1) 3.35 (5)

38 Anhang 215 Table 3a: Bond lengths [Å]. Numbers in parentheses are estimated standard deviations in the least significant digits. Si1-O (1) C5-C (2) Si1-C (2) C6-C (3) Si1-C (2) C6-C (3) Si1-C (2) C7-C (3) Si2-O (2) C8-C (3) Si2-C (2) C8-C (3) Si2-C (2) C9-C (3) Si2-C (2) C10-C (3) O1-C (2) C11-C (3) O2-C (2) C11-C (3) O3-C (2) C12-C (3) O4-C (2) C16-C (3) O5-C (2) C16-C (3) N1-C (2) C17-C (3) N1-C (3) C18-C (3) N1-C (2) C19-C (3) N2-C (2) C20-C (3) N2-C (2) C25-C (3) N2-C (2) C25-C (3) C2-C (3) C25-C (3) C2-C (3) C32-C (3) C3-C (3) C32-C (3) C4-C (3) C32-C (3) C5-C (3)

39 Anhang 216 Table 3b: Bond angles [deg]. O4-Si1-C (9) C5-C6-C (1) O4-Si1-C (8) C7-C6-C (1) O4-Si1-C (8) C6-C7-C (1) C23-Si1-C (1) C7-C8-C (2) C23-Si1-C (1) C7-C8-C (1) C24-Si1-C (1) C9-C8-C (1) O5-Si2-C (9) C8-C9-C (2) O5-Si2-C (1) O4-C10-C (2) O5-Si2-C (8) O4-C10-C (2) C30-Si2-C (1) C9-C10-C (1) C30-Si2-C (1) C10-C11-C (2) C31-Si2-C (1) C10-C11-C (2) Si1-O4-C (1) C12-C11-C (1) Si2-O5-C (1) C8-C12-C (1) C1-N1-C (1) C8-C12-C (1) C1-N1-C (2) C11-C12-C (1) C2-N1-C (2) C6-C13-C (1) C1-N2-C (1) C3-C16-C (2) C1-N2-C (2) C3-C16-C (2) C3-N2-C (1) C17-C16-C (2) O1-C1-N (2) C16-C17-C (2) O1-C1-N (2) C17-C18-C (2) N1-C1-N (2) C18-C19-C (2) N1-C2-C (1) C19-C20-C (2) N1-C2-C (2) C16-C21-C (2) C3-C2-C (2) Si1-C25-C (1) N2-C3-C (1) Si1-C25-C (1) N2-C3-C (2) Si1-C25-C (2) C2-C3-C (1) C26-C25-C (2) O2-C4-N (2) C26-C25-C (2) O2-C4-C (2) C27-C25-C (2) N2-C4-C (2) O5-C29-C (1) C4-C5-C (1) Si2-C32-C (1) C4-C5-C (1) Si2-C32-C (1) C6-C5-C (1) Si2-C32-C (1) O3-C6-C (1) C33-C32-C (2) O3-C6-C (1) C33-C32-C (2) O3-C6-C (1) C34-C32-C (2) C5-C6-C (1)

40 Anhang 217 Table 4: Anisotropic displacement parameters (Å 2 ). The form of the anisotropic displacement parameter is: exp [ -2π 2. ( h 2. a 2. U 11 + k 2. b 2. U 22 + l 2. c 2. U h. k. a. b. U h. l. a. c. U k. l. b. c. U 23 )] where a, b, and c are reciprocal lattice constants. U11 U22 U33 U23 U13 U12 Si (2) (2) (2) (2) (2) (2) Si (2) (2) (2) (2) (2) (2) O (6) (7) (6) (6) (5) (6) O (6) (7) (6) (6) (5) (6) O (7) (6) (5) (6) (5) (5) O (7) (7) (6) (6) (5) (5) O (8) (7) (6) (6) (6) (6) N (7) (7) (7) (6) (6) (6) N (7) (7) (6) (6) (6) (6) C (8) (8) (8) (7) (7) (7) C (9) (9) (8) (8) (7) (8) C (8) (9) (7) (7) (7) (8) C (8) (8) (8) (7) (7) (7) C (8) (8) (8) (7) (7) (7) C (8) (8) (7) (7) (7) (7) C (8) (9) (8) (7) (7) (7) C (8) (9) (8) (8) (7) (8) C (8) (1) (8) (9) (7) (9) C (9) (9) (9) (8) (7) (8) C (9) (8) (8) (8) (7) (7) C (9) (9) (7) (7) (7) (7) C (8) (8) (8) (7) (7) (7) C (1) (1) (9) (8) (8) (8) C (1) (1) (9) (9) (8) (9) C (9) (8) (8) (8) (7) (7) C (1) (1) (9) (9) (8) (9) C (1) (1) (9) (1) (9) (1) C (1) (1) (9) (1) (1) (9) C (1) (1) (9) (9) (9) (8) C (9) (9) (9) (8) (8) (8) C (9) (9) (8) (8) (7) (8) C (1) (1) (1) (1) (1) (1) C (1) (1) (9) (1) (9) (9) C (1) (1) (9) (9) (8) (8) C (2) (1) (1) (1) (1) (1) C (1) (1) (1) (1) (1) (1) C (1) (1) (9) (1) (9) (1) C (1) (9) (9) (9) (9) (8)

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